Kylie Jenner’s Blue Ferrari, Chanel Backpack & High-Top Sneakers Steal the Spotlight

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Just weeks after her split from Tyga, Kylie Jenner proved she was moving on in style. In May 2016, the then-18-year-old reality star stepped out for some retail therapy at Planet Blue in Malibu, turning heads with her laid-back, luxe streetwear look.

With her signature blend of high-end accessories and casual pieces, Kylie made it clear she wasn’t letting a breakup dull her shine.

Kylie Jenner keeps it casual in a teal "Life of Pablo" tee, denim cut-offs, and white Chanel high-top sneakers while shopping in Malibu on May 27, 2016Kylie Jenner keeps it casual in a teal “Life of Pablo” tee, denim cut-offs, and white Chanel high-top sneakers while shopping in Malibu on May 27, 2016 (Credit: WENN)

Kylie Jenner’s Vintage Chanel Backpack Steals the Spotlight

The American reality television personality accessorized her casual ensemble — an oversized Life of Pablo t-shirt and denim shorts — with some vintage pieces from Chanel.

Kylie Jenner's white vintage Chanel backpackKylie Jenner’s white vintage Chanel backpack (Credit: WENN)

This is not the first time we’ve seen her carrying this vintage bag.

Kylie Jenner's white vintage Chanel backpack featuring a drawstring closure with gold-tone hardware, a tonal designer logo detail, a rear zip pocket, and two leather shoulder strapsKylie Jenner’s white vintage Chanel backpack featuring a drawstring closure with gold-tone hardware, a tonal designer logo detail, a rear zip pocket, and two leather shoulder straps (Credit: WENN)

She posted a selfie showcasing the purse, a part of her enviable backpack collection, on Instagram a couple of months ago.

Kylie Jenner showing off her Chanel backpack with momager Kris JennerKylie Jenner showing off her Chanel backpack with momager Kris Jenner on February 6, 2016 (Credit: Kylie Jenner’s Instagram)

The Blue Ferrari That Made Headlines

She also shared an Instagram photo wearing a ‘Life of Pablo’ t-shirt while posing next to the birthday gift from her former beau.

Kylie Jenner wears a "Life of Pablo" t-shirt to show off her blue FerrariKylie Jenner wears a “Life of Pablo” t-shirt to show off her blue Ferrari (Credit: Kylie Jenner’s Instagram)

The 18-year-old American reality television personality, socialite, and model posed in front of her $260,000 Ferrari — yes, the white one Tyga gifted her for her 18th birthday — that she recently had painted blue.

Kylie Jenner's foundation contrasts her pale skin as she admires her new blue FerrariKylie Jenner’s foundation contrasts with her pale skin as she admires her new blue Ferrari (Credit: WENN)

Casual Street Style: T-Shirt, Shorts, and Chanel Sneakers

Kylie was later seen shopping with friends at Planet Blue.

Kylie Jenner wears an oversize blue t-shirt and sneakers as she shops with friends in MalibuKylie Jenner wears an oversized blue t-shirt and sneakers as she shops with friends in Malibu (Credit: WENN)

Makeup Mishap or Lighting Fluke?

For all the color-coordinating she did, Kylie seemed to miss the opportunity to match her makeup.

Kylie Jenner shops with friends in an oversized blue t-shirt and denim cut-offsKylie Jenner shops with friends in an oversized blue t-shirt and denim cut-offs (Credit: WENN)

From some angles, her foundation appeared several shades darker than her neck — was it a makeup mishap or just unflattering lighting?

Kylie Jenner shops with friends in an oversized blue t-shirt and denim cut-offsKylie Jenner shops with friends in an oversized blue t-shirt and denim cut-offs (Credit: WENN)

Ostentatious lifestyle and poor makeup blending aside, it was refreshing to see Kylie dressed in a regular t-shirt, denim shorts, and sneakers, like a typical teenager.

Kylie Jenner accessorizes with sunglasses and bracelets during a Malibu shopping tripKylie Jenner accessorizes with sunglasses and bracelets during a Malibu shopping trip (Credit: WENN)

Chanel Sneakers Take Center Stage

It was also lovely to see her just kickin’ it and having fun with her non-Hollywood friends.

Kylie Jenner wears Chanel sneakers with a casual shorts-and-tee lookKylie Jenner wears Chanel sneakers with a casual shorts-and-tee look (Credit: WENN)

At the time, Kylie was just 18 years old—already a Lip Kit creator and rising fashion mogul.

Kylie Jenner's feet in white Chanel zip-top sneakersKylie Jenner’s feet in white Chanel zip-top sneakers (Credit: WENN)

Kylie Jenner felt blue in these retro-inspired Chanel zip high-top sneakers.

White Chanel Zip High-Top SneakersWhite Chanel Zip High-Top Sneakers

You can achieve a similar look for just $69.95 with Steve Madden’s “Decaf” sneakers, available for order at Zappos.

White Steve Madden "Decaf" SneakersWhite Steve Madden “Decaf” Sneakers, $69.95

At first glance, the Kardashian-Jenner family and the house of Chanel might seem like cultural opposites—one thrives on reality TV and social media spectacle, the other on heritage, exclusivity, and refined taste.

Yet, despite their starkly different brand identities, both are undisputed powerhouses in shaping the fashion and pop culture landscape. And when these two forces collide, the results are always headline-worthy.

Chanel Moments: Kardashian-Jenner Style Icons in the Iconic Brand

The Kardashian-Jenner clan has long been associated with high fashion, and Chanel remains a staple in their wardrobes. Here are some standout moments where they showcased their love for the iconic brand:

Kendall Jenner’s Chanel Runway Appearance

Kim Kardashian’s Barbie-Inspired Pink Chanel Cardigan

Kourtney Kardashian’s Chic Chanel Waist Bag

Kris Jenner’s Chanel Perfume Bottle Bag

These moments highlight the family’s enduring relationship with Chanel, showcasing how each member incorporates the brand’s timeless pieces into their unique styles.